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在碱存在下通过臭氧对邻苯二酚的氧化高效合成衣康酸。

Efficient Synthesis of ,-Muconic Acid by Catechol Oxidation of Ozone in the Presence of a Base.

作者信息

Katayama Kohtaro, Hotta Hiroki, Tsujino Yoshio

机构信息

Graduate School of Maritime Sciences, Kobe University, 5-1-1 Fukae-minami, Kobe 658-0022, Hyogo, Japan.

Graduate School of Science, Technology and Innovation, Kobe University, 1-1, Rokkodai, Kobe 657-0013, Hyogo, Japan.

出版信息

Molecules. 2025 Jan 6;30(1):201. doi: 10.3390/molecules30010201.

DOI:10.3390/molecules30010201
PMID:39795257
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11721871/
Abstract

Muconic acid, a crucial precursor in synthesizing materials like PET bottles and nylon, is pivotal for the anticipated growth in the textiles and plastics industries. This study presents a novel chemical synthesis route for ,-muconic acid (ccMA) using catechol. Biochemical methods face scale-up challenges due to microorganism sensitivity and complex extraction processes, while chemical methods involve environmentally harmful substances and have low yields. Our research introduces a method that enhances ccMA yield to 56% by employing ozonation in the presence of an alkali, significantly simplifying the synthesis process. This one-step synthesis reduces reagent use and labor, aligns with green chemistry principles, and avoids using toxic chemicals. The methodology, involving the low-temperature ozonation of catechol with base addition, reduces ccMA degradation and improves yield, as confirmed by an HPLC analysis and replicated experiments. This promising approach could lead to sustainable industrial synthesis of muconic acid derivatives. Further investigations will focus on refining this method for larger-scale applications and testing its economic viability, aiming to optimize conditions for maximum efficiency and yield.

摘要

粘康酸是合成PET瓶和尼龙等材料的关键前体,对纺织和塑料行业的预期增长至关重要。本研究提出了一种使用儿茶酚合成反,反-粘康酸(ccMA)的新型化学合成路线。由于微生物敏感性和复杂的提取过程,生化方法面临扩大规模的挑战,而化学方法涉及环境有害物质且产率较低。我们的研究引入了一种方法,通过在碱存在下进行臭氧化,将ccMA产率提高到56%,显著简化了合成过程。这种一步合成减少了试剂使用和劳动力,符合绿色化学原则,避免使用有毒化学品。经高效液相色谱分析和重复实验证实,该方法通过在低温下对儿茶酚进行碱添加臭氧化,减少了ccMA的降解并提高了产率。这种有前景的方法可能会实现粘康酸衍生物的可持续工业合成。进一步的研究将集中于改进该方法以用于大规模应用并测试其经济可行性,旨在优化条件以实现最高效率和产率。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d700/11721871/75469dca29d4/molecules-30-00201-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d700/11721871/316c2d3dc253/molecules-30-00201-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d700/11721871/573a70eda8a0/molecules-30-00201-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d700/11721871/cc3257a788eb/molecules-30-00201-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d700/11721871/75469dca29d4/molecules-30-00201-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d700/11721871/316c2d3dc253/molecules-30-00201-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d700/11721871/573a70eda8a0/molecules-30-00201-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d700/11721871/cc3257a788eb/molecules-30-00201-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d700/11721871/75469dca29d4/molecules-30-00201-sch004.jpg

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